EP3114104B1 - Procédé de préparation de menthones à partir de l'isopulégol en phase gazeuse - Google Patents

Procédé de préparation de menthones à partir de l'isopulégol en phase gazeuse Download PDF

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Publication number
EP3114104B1
EP3114104B1 EP15707978.1A EP15707978A EP3114104B1 EP 3114104 B1 EP3114104 B1 EP 3114104B1 EP 15707978 A EP15707978 A EP 15707978A EP 3114104 B1 EP3114104 B1 EP 3114104B1
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Prior art keywords
copper
catalyst
oxide
process according
isopulegol
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German (de)
English (en)
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EP3114104A1 (fr
Inventor
Volker Hickmann
Stefan Rüdenauer
Martine DEHN
Andreas Keller
Stephanie RENZ
Daniel Schneider
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BASF SE
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
    • B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
    • B01J23/76—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
    • B01J23/84—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36 with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
    • B01J23/889—Manganese, technetium or rhenium
    • B01J23/8892—Manganese
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
    • C07C45/298—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups with manganese derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
    • C07C49/407—Menthones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/10—General cosmetic use
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Definitions

  • Enantiomerically pure means that in addition to the specifically designated enantiomer no further enantiomeric form of the same chemical compound with at least one center of asymmetry is analytically detectable.
  • the proportion of copper compounds in the catalyst is at least 20 to 100% based on the total weight of the dry catalyst.
  • the proportion of copper compounds in the catalyst is 25 to 95%, e.g. 30-65%, in particular 30-45%, based on the total weight of the dry catalyst.
  • hexanol includes the diols 1,2-hexanediol, 1,3-hexanediol, 1,4-hexanediol, 1,5-hexanediol, 1,6-hexanediol, 2,3-hexanediol, 2,4-hexanediol, 2,5-hexanediol and 3,4-hexanediol, and the branched structural isomers thereof.
  • the product mixture was condensed at the reactor outlet and the composition analyzed by gas chromatography. After a test time of five hours in each case, the reactor and the evaporator were cooled under a stream of nitrogen (20 NL / h) and the experiment was continued after 18 h without a catalyst change.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Dermatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Catalysts (AREA)
  • Cosmetics (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Seasonings (AREA)
  • Medicinal Preparation (AREA)

Claims (15)

  1. Procédé de mise en réaction d'isopulégol pour former de la menthone, selon lequel l'isopulégol est mis en contact dans une phase de gaz vecteur avec un catalyseur à base de cuivre oxydique activé, contenant éventuellement au moins un élément supplémentaire choisi parmi l'aluminium, le manganèse, le baryum, le chrome, le calcium et le fer, et un produit de réaction contenant de la menthone est éventuellement isolé après la réaction, la réaction ayant lieu à une température de 150 à 250 °C.
  2. Procédé selon la revendication 1, selon lequel le catalyseur à base de cuivre est activé avec de l'hydrogène ou de l'hydrogène et un alcool.
  3. Procédé selon la revendication 1 ou 2, selon lequel le cuivre se présente au niveau d'oxydation +I ou +II dans le catalyseur à base de cuivre oxydique.
  4. Procédé selon les revendications 1 à 3, selon lequel le gaz vecteur comprend de l'azote, de l'argon ou un mélange de ceux-ci.
  5. Procédé selon l'une quelconque des revendications précédentes, selon lequel l'isopulégol utilisé comprend un énantiomère de formule I
    Figure imgb0017
  6. Procédé selon l'une quelconque des revendications précédentes, selon lequel la réaction est réalisée à une température de 160 à 200 °C, notamment de 160 à 190 °C.
  7. Procédé selon l'une quelconque des revendications précédentes, selon lequel le catalyseur à base de cuivre comprend du cuivre et un élément supplémentaire choisi parmi l'aluminium, le manganèse, le baryum, le chrome, le calcium et le fer sous forme élémentaire et/ou sous la forme d'oxydes.
  8. Procédé selon la revendication 7, selon lequel les oxydes se présentent sous la forme d'oxydes d'un élément, d'oxydes doubles et/ou d'oxydes multiples.
  9. Procédé selon l'une quelconque des revendications précédentes, selon lequel le catalyseur à base de cuivre présente une proportion d'au moins 20 % à 100 % en poids de composé de cuivre par rapport à la masse sèche du catalyseur.
  10. Procédé selon l'une quelconque des revendications précédentes, selon lequel le catalyseur à base de cuivre est choisi parmi les catalyseurs ayant les compositions suivantes :
    a) 30 à 40 % d'oxyde de cuivre, 10 à 25 % d'oxyde d'aluminium, 10 à 25 % d'oxyde de manganèse et 30 à 40 % d'oxyde d'aluminium et de cuivre,
    b) 30 à 45 % d'oxyde de cuivre, 10 à 25 % d'oxyde d'aluminium, 10 à 20 % d'oxyde de manganèse et 30 à 40 % d'oxyde d'aluminium et de cuivre,
    c) 60,0 à 65,0 % d'oxyde de chrome et de cuivre (Cr2CuO4), 20,0 à 25,0 % d'oxyde de cuivre, 5,0 à 10,0 % d'oxyde de baryum, 1,0 à 5,0 % de graphite, 1,0 % de trioxyde de dichrome et 1,0 % de trioxyde de chrome,
    d) 60,0 à 70,0 % d'oxyde de chrome et de cuivre (Cr2CuO4), 20,0 à 30,0 % d'oxyde de cuivre, 1,0 à 5,0 % de dioxyde de manganèse, 1,0 à 5,0 % de silice (sel de sodium), 1,0 à 5,0 % de graphite et 0,0 à 0,5 % de chromate de cuivre,
    e) 55,0 à 65,0 % d'oxyde de chrome et de cuivre (Cr2CuO4), 20,0 à 30,0 % d'oxyde de cuivre, 5,0 à 10,0 % de dioxyde de silicium, 5,0 à 10,0 % de silice (sel de sodium) et 1,0 à 5,0 % de graphite,
    f) 41,0 à 46,0 % d'oxyde de chrome et de cuivre (Cr2CuO4), 25,0 à 35,0 % d'oxyde d'aluminium, 13,0 à 17,0 % d'oxyde de cuivre et 10,0 à 13,0 % de chromate de baryum,
    g) 55,0 à 65,0 % d'oxyde de cuivre, 25,0 à 35,0 % de silicate de calcium, 5,0 à 10,0 % de palygorskite ([Mg(Al0,5-1Fe0-0,5)]Si4(OH)O10,4H2O), 1,0 à 5,0 % de graphite, 1,0 à 5,0 % de dioxyde de silicium et 0,5 à 1,5 % de silice (cristalline), et
    h) un mélange de celles-ci,
    à chaque fois en % en poids par rapport à la masse sèche du catalyseur.
  11. Procédé selon l'une quelconque des revendications précédentes, selon lequel le catalyseur est activé avant la réaction avec de l'hydrogène et un alcool simultanément ou en décalage dans le temps dans un ordre quelconque, éventuellement dans un courant de gaz vecteur.
  12. Procédé selon la revendication 11, dans lequel le gaz vecteur est l'azote ou l'argon, et contient éventuellement jusqu'à 10 % en volume d'hydrogène.
  13. Procédé selon l'une quelconque des revendications précédentes, selon lequel l'alcool utilisé pour l'activation est choisi parmi les mono- ou polyols saturés ou mono- ou polyinsaturés, linéaires ou ramifiés ou cycliques, aliphatiques ou aromatiques, notamment les mono- ou diols, ou les combinaisons de ceux-ci.
  14. Procédé selon l'une quelconque des revendications précédentes, selon lequel l'alcool utilisé pour l'activation comprend au moins un groupe OH primaire et/ou secondaire.
  15. Procédé de fabrication d'un produit choisi parmi les produits alimentaires, les produits cosmétiques, les produits pharmaceutiques, les formulations de tabac, les produits ménagers et les produits d'entretien du linge, selon lequel un additif contenant de la menthone est fabriqué par un procédé selon les revendications 1 à 14, et cet additif est ajouté au produit.
EP15707978.1A 2014-03-07 2015-03-06 Procédé de préparation de menthones à partir de l'isopulégol en phase gazeuse Active EP3114104B1 (fr)

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EP14158373.2A EP2915797A1 (fr) 2014-03-07 2014-03-07 Procédé de préparation de menthones à partir de l'isopulégol en phase gazeuse
PCT/EP2015/054693 WO2015132370A1 (fr) 2014-03-07 2015-03-06 Procédé de préparation de menthones à partir d'isopulégol en phase gazeuse

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US (1) US9856199B2 (fr)
EP (3) EP2915797A1 (fr)
JP (1) JP6580605B2 (fr)
CN (1) CN106061933B (fr)
ES (2) ES2750313T3 (fr)
MX (1) MX2016011621A (fr)
WO (1) WO2015132370A1 (fr)

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CN107438600B (zh) 2015-03-05 2021-04-13 巴斯夫欧洲公司 制备四氢吡喃基酯的方法
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PL3319951T3 (pl) 2015-07-10 2022-02-28 Basf Se Sposób hydroformylowania 2-podstawionych butadienów oraz wytwarzania ich produktów pochodnych, w szczególności ambroksu
CN107848930A (zh) 2015-07-15 2018-03-27 巴斯夫欧洲公司 制备芳基丙烯的方法
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Publication number Publication date
EP2915797A1 (fr) 2015-09-09
CN106061933A (zh) 2016-10-26
US9856199B2 (en) 2018-01-02
ES2750313T3 (es) 2020-03-25
WO2015132370A1 (fr) 2015-09-11
ES2965627T3 (es) 2024-04-16
MX2016011621A (es) 2016-12-14
JP2017514886A (ja) 2017-06-08
EP3539942B1 (fr) 2023-09-13
EP3539942A1 (fr) 2019-09-18
US20170066705A1 (en) 2017-03-09
CN106061933B (zh) 2019-07-09
JP6580605B2 (ja) 2019-09-25
EP3114104A1 (fr) 2017-01-11
EP3539942C0 (fr) 2023-09-13

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